Sam: Dad said they always had the perfect marriage.
Dean: It wasn't perfect until after (Mary) died.

Sam: Heaven?
Dean: Yeah.
Sam: Okay, how are we in Heaven?
Dean: All that clean living, I guess.

Go ahead, Roy. Do it. But I'm gonna warn you--when I come back, I'm gonna be pissed.

Dean

What are you, the Hamburglar?

Dean

Why does Heaven care if Harry meets Sally?

Dean

Unleash the Kraken. See you tomorrow morning.

Sam

Dean: Hey, when I want to drink, I drink. When I want sex, I go get it. Same goes for a sandwich or a fight.
Castiel: So... you're saying you're just well-adjusted?
Dean: God, no. I'm just well-fed.

Sam: Dean, enough!
Dean: What?
Sam: You just punched a Cupid!
Dean: I punched a dick!

Cupid: Love is more than a word to me, you know? I love love, I love it! And if that's wrong, I don't want to be right!
Castiel: Yes, yes. of course. I, uh... I have no idea what you're saying.

Dean: Cherub?
Castiel: Yeah, they're all over the world. There are dozens of them.
Dean: You mean the little flying fat kids in diapers?
Castiel: They're not incontinent.

Dean: Where am I going?
Sam: Dean, it's Valentine Day. Your favorite holiday, remember? I mean, what do you always call it - uh, Unattached Drifter Christmas?

Castiel: This is their handshake.
Dean: I don't like it.
Castiel: No one likes it.

Supernatural Season 5 Quotes

So what's it all add up to? It's hard to say. But me, I'd say this was a test... for Sam and Dean. And I think they did all right. Up against, Good, Evil, angels, devils, Destiny, and God himself, they made their own choice. They chose family. And, well... isn't that kinda the whole point? No doubt - endings are hard. But then again... nothing ever really ends, does it?

Chuck

Dean: Dude, he's short.
Sam: Hey, Gandhi was a great man.
Dean: For a Smurf.